Winter Vacations from $946

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The Latest Winter vacation packages

Price found within the past 48 hours. Click for updated prices.
Indianhead Ironwood Motel

Indianhead Ironwood Motel

2.5 out of 5
Price was $1,021, price is now $946 per person
$946
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Allentown (ABE) to Ironwood (IWD)
8/10 Very Good! (304 reviews)
Clean rooms. Outdated roadside motel, but Great price.

Reviewed on Feb 28, 2026

Snow Chasers Lodge

Snow Chasers Lodge

3.5 out of 5
Price was $1,066, price is now $1,000 per person
$1,000
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Allentown (ABE) to Ironwood (IWD)
8/10 Very Good! (81 reviews)
Parking was great! I liked the online check-in process. We enjoyed the lounge upstairs.

Reviewed on Mar 3, 2026

Snowriver Mountain Resort

Snowriver Mountain Resort

2.5 out of 5
Price was $1,085, price is now $1,030 per person
$1,030
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Allentown (ABE) to Ironwood (IWD)
8.2/10 Very Good! (269 reviews)
Nice place. Quiet. Not as nice as photos make it out to be, but still worth the visit. No frills.

Reviewed on Jan 26, 2026

AmericInn by Wyndham Silver City

AmericInn by Wyndham Silver City

2.5 out of 5
Price was $1,104, price is now $1,052 per person
$1,052
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Allentown (ABE) to Ironwood (IWD)
9/10 Wonderful! (1,003 reviews)
The room was clean and modernized. The front desk staff coming and going were cheerful and helpful. It was a nice stay.

Reviewed on Feb 11, 2026

AmericInn by Wyndham Ironwood

AmericInn by Wyndham Ironwood

2.5 out of 5
Price was $1,224, price is now $1,195 per person
$1,195
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Allentown (ABE) to Ironwood (IWD)
9/10 Wonderful! (786 reviews)
Clean and quiet. Close to Big Powderhorn.

Reviewed on Mar 8, 2026

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Winter Hotel Deals

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

Loretta WI
10/10 Exceptional! (21 reviews)
Cabin was very comfortable and clean, and host was very responsive, we had a great stay!

Reviewed on Mar 12, 2026

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EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

Loretta WI
$557 nightly
The price is $588 total per night from Mar 18 to Mar 19
$588 total
Mar 18 - Mar 19
Total with taxes and fees
10/10 Exceptional! (3 reviews)
Perfect for a group
This cabin is perfect for a group! The listing was exactly as described, beautiful property, and the lake is not busy. The host responds quickly and everything went great!

Reviewed on Jul 28, 2025

The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!
Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

2.5 out of 5
15586 County Road B Hayward WI
Fully refundable
$119 nightly
The price is $130 total per night from Apr 12 to Apr 13
$130 total
Apr 12 - Apr 13
Total with taxes and fees
9.6/10 Exceptional! (662 reviews)
Nice clean room and decent breakfast

Reviewed on Mar 9, 2026

Holiday Inn Express & Suites Hayward by IHG
See all 680 properties in Winter
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Winter Vacation Packages

Winter Essential Information

Language
English
Currency
U.S dollars
Population
310

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Frequently asked questions

How much does a Winter vacation package cost?
You can pick up a vacation package to this popular destination from $946 on Expedia. But how much your vacation to Winter costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winter?
February, September and November are the best times to search for cheap Winter vacation packages. Traveling in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Winter?
With a well-planned itinerary, you can easily hit the main Winter sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Winter vacation for longer.
How to find the best Winter package deals?
Bagging a cheap Winter package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Winter package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winter vacation as a package?
You can enjoy significant savings on your Winter escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter?
If you've got your Winter travel dates locked in, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winter vacation packages?
Jet off on your dream trip to Winter with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.